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<h1><a href="https://archiveofourown.org/works/27598412">Gun Smoke and Hickeys</a> by <a class='authorlink' href='https://archiveofourown.org/users/jantolover/pseuds/jantolover'>jantolover</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Alternate Universe - BDSM, Alternate Universe - Human, Alternate Universe - Mob, Alternate Universe- No Supernatural, Anal Sex, Angst, Angst and Feels, Angst and Fluff and Smut, Angst and Porn, Angst and Romance, BDSM, Big Gay Mobsters, Blood and Violence, Bondage, Bondage and Discipline, Bottom Dean Winchester, Butt Slapping, Castiel Talks Dirty (Supernatural), Castiel/Dean Winchester BDSM, Condoms, Consensual But Not Safe Or Sane, Crime Scenes, Daddy Dom Castiel (Supernatural), Daddy Kink, Dean Winchester Talks Dirty, Dirty Talk, Dirty Thoughts, Dom Castiel (Supernatural), Dom Castiel/Sub Dean Winchester, Dom Lisa Braeden, Dom/sub, Eventual Fluff, Eventual Smut, F/M, Face Slapping, Fluff, Fluff and Angst, Fluff and Smut, Gay Sex, Gentle Dom Castiel (Supernatural), Gratuitous Smut, Gun Violence, Hair-pulling, Heavy Angst, Heavy BDSM, Homophobia, Light Angst, Light BDSM, Light Bondage, M/M, Master/Slave, Mild Smut, Minor Lisa Braeden/Dean Winchester, Murder, Non-Graphic Smut, Oral Sex, Painplay, Pegging, Period-Typical Homophobia, Prostate Massage, Prostate Milking, Robbery, Romantic Fluff, Rope Bondage, Rough Oral Sex, Rough Sex, Safe Sane and Consensual, Sex, Sexy Times, Shameless Smut, Slapping, Slow Burn, Smut, Sub Dean, Sub Dean Winchester, Tooth-Rotting Fluff, Top Castiel (Supernatural), Unsafe Sex, Vaginal Sex, Violence</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>In-Progress</td></tr>

<tr><td><b>Published:</b></td><td>2020-11-17</td></tr>

<tr><td><b>Updated:</b></td><td>2021-02-21</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-07 00:35:26</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Graphic Depictions Of Violence</td></tr>

<tr><td><b>Chapters:</b></td><td>9</td></tr>

<tr><td><b>Words:</b></td><td>4,435</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27598412</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/jantolover/pseuds/jantolover</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>1952. Elvis, black and white TV, cigarettes are "healthy" Charles Manson and his family, and the mob.</p>
<p>Dean Winchester was a good kid. He was a star student, had friends, a loving girlfriend, and stayed out of trouble. That is, until he met bad-boy-to-a-point Castiel Novak.</p>
<p>Castiel Novak never imagined himself a son of the mob. When his birth parents beat him and kicked him to the curb for kissing a boy, he soon feared for his life on the street. That's where he met a mysterious man. He was taken in by the mob. He belonged, he was loved, and he was cared for.</p>
<p>By chance, Dean ran into Castiel, or Cas or Cassie by his family. He was immediately infatuated with the mysterious boy. He fell head over heels.</p>
<p>Cassie didn't want to be involved with Dean, thinking a younger man would want nothing to do with the lifestyle. That all changed when Dean murdered his own girlfriend for him.</p>
<p>The two become inseparable.</p>
<p>God help those who cross the prince and his special boy.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel &amp; Dean Winchester, Castiel &amp; Kevin Tran, Castiel/Dean Winchester, Castiel/Kevin Tran, John Winchester/Mary Winchester, Lisa Braeden &amp; Dean Winchester, Lisa Braeden/Dean Winchester</td></tr>

<tr><td><b>Kudos:</b></td><td>39</td></tr>

</table>

<a name="section0001"><h2>1. 1</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Castiel met James in school. It was not love at first sight, no. That only exists in faerie tales. It took about four months for them to fall in love. </p><p>Although that seems fast, they spent nearly every waking (and slumbering) moment together. They were immediate best friends who walked to class, ate lunch, and did homework after school every day together.</p><p>James made the first move. On the last day of their senior year, they cut their last two periods because fuck it.</p><p>"We're going to get in trouble" Castiel laughed as he let James pull him behind the school. His laugh was immediately cut off when James pressed him against the wall.</p><p>"I love you" James said after he kissed him.</p><p>They took turns sneaking out and sleeping next to each other every night.</p><p>They didn't need to have sex to know they were inseparable.</p><p>There were constant whispers, but nobody asked about their relationship.</p><p>Then they were caught.</p><p>In 1947, after James and Castiel were sneaking around for about ten months (or nine- it depends on if you round up or down) a young girl caught them.</p><p>She shouldn't-- couldn't have understood the truly awful things she said.</p><p>The couple screamed back at her in pain, fear, and anger all at once.</p><p>The raucous caused a crowd to form. Some asked what happened, some just listened.</p><p>The child pointed at James and Castiel. "There is 'um queers sinnin' in da streets!"</p><p><em>"Fucking </em><em>faggots</em><em>!" </em>a large woman who could use Castiel as a toothpick spat on James's face.</p><p>The couple looked at each other for the last time and bolted.</p><p>Castiel just ran. He didn't think where to, he just ran. He ended up at home. He never saw James again.</p><p>⚫⚫⚫⚫</p><p>The officer came late that night. Castiel was sleeping when his furious father screamed at him from the kitchen. He jumped up out of bed like a bunny and practically flew to the kitchen.</p><p>Chuck looked like he was ready to kill his only child. "You kissed a boy?"</p><p>The question was more of a threat.</p><p>Castiel did not answer.</p><p>Chuck grabbed him by his shirt collar and pulled him close to his face. <em>"Did you fucking kiss a boy?"</em></p><p>"Yes" Cas said meekly.</p><p>The first blow was a huge shock to him. After the third, he started to beg for him to stop. After the sixth or seventh hit, Cas realized it wasn't just discipline and round punched his father's cheek.</p><p>Cas ran before the blood and teeth hit the floor.</p><p>👊👊👊👊</p><p>Dean met Lisa in jail. Now, it's not what you think. Dean Winchester was a star student. He stayed out of trouble. So how the hell did he end up in jail? He volunteered their.</p><p>The only child of the Winchester house volunteered just about anywhere. Why? Because it fell good to help. No, he was not an acting officer, but he cleaned and cooked and went home.</p><p>Lisa Breadon was charged with petty theft on July eighteenth, 1950. She came in quiet and small. Dean almost immediately caught her eye. They snuck in conversations the entire day, and made love at her house all night. Only after she paid her fine, of course.</p><p> </p>
  </div></div>
<a name="section0002"><h2>2. 2</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>The dark man didn't speak. He only approached a dirty and starving Castiel.</p>
<p>When Cas realized he wouldn't leave, he looked up at him. He took his hand when he offered, and let himself be lead up.</p>
<p>The man dropped his hand and continued to walk.</p>
<p>Cas followed. "Where are you taking me?" Castiel's dry throat managed to spit out.</p>
<p>"Home, my child". The man was considerably shorter than him and spoke with a British accent. If he was ten years younger, Cas would have called him hot.</p>
<p>"Why are you doing this?" The hot British man looked at him. "I have absolutely no fucking idea" he said. "I just couldn't stand seeing you like this".</p>
<p>"Are you going to hurt me?"</p>
<p>He shook his head. "Why would I do that?"</p>
<p>Cas was stumped. His face furrowed. "Then what do you want?"</p>
<p>"I want you to be safe, my child".</p>
<p>Castiel was not convinced. "What's the catch?"</p>
<p>Hot British Man took a breath. He turned to Cas. "Let's get home first" he said. "I'll explain everything".</p>
  </div></div>
<a name="section0003"><h2>3. 3</h2></a>
<div class="story"><div class="userstuff module">
    
    <p></p><div>
  <p>
    <br/>
    <b>Five Years </b>
    <b>Later</b>
  </p>
</div><p> </p><p></p><div>
  <p>Dean wrapped his bare legs around Lisa tighter. He watched her naked breasts jiggle and bounce as she thrusts harder and took his hand to her clit.</p>
  <p>He obeyed and massaged it.</p>
  <p><em>"Fuck! </em>Good boy, Dean. Play with Mommy's sweet spot".</p>
  <p>Dean pressed his fingers harder against the small and sensitive bulb. He quickly rubbed it back and forth with the middle. He pinched it with his middle finger and thumb and pulled slowly from the inside to the out. He slid up and pulled down slower. Again, but slower than that. Even slower than before. He rubbed the end of it quickly, then slowly, then quickly again.</p>
  <p>Lisa screamed as she came all over Dean's fingers and a little on his stomach. She raised her hips and Dean's red, hard, throbbing dick twitched in the condom and he squirted with a whore- ish moan. Lisa jacked him off until the latex was full and Dean's balls were empty.<br/>Dean panted heavily and let out a sensitive whine when his mistress removed the protection and licked the cum that managed to get on his dick.</p>
  <p><em>"Oh! Mommy!</em>"</p>
  <p>"Good boy. Good boy, Dean".</p>
  <p>🍑🍆🍌💧👅👉👌</p>
  <p>Five years in the mob can make a scared, starving boy a ruthless, dangerous man.</p>
  <p>Castiel forgot, or rather pretended that he forgot, his parents. Fergus "Crowley" McCloud was his parent. Well, he was a son of the mob and Crowley took him in.</p>
  <p>Five years can be a long time. Cas became a new person completely. He was barely, if not, his old self. Cas was desensitized by his family. He didn't care what he did. Or even <em>who</em> he did.</p>
  <p>
    <em>"Oh fuck, Cassie!"</em>
  </p>
  <p>Cas rocked his hips harder into his "brother".</p>
  <p><em>"Yeah? You like that?"</em> Cas asked Kevin.</p>
  <p>"Yeah. Fuck, baby! <em>Right there</em>!"</p>
  <p>Cassie continued to ram the twink's prostate.</p>
  <p>
    <em>"I'm close!"</em>
  </p>
  <p>"Me too, Baby. Where do you want it?"</p>
  <p>"On my face! Let me swallow it!"</p>
  <p><em>"Fuck" </em>Cas pulled out of the tan ass and flipped his submissive around. He forced him on the floor on his knees in front of him.</p>
  <p>"You want this dirty load, <em>you little slut</em>?" Cas slapped his face with his long and fat cock.</p>
  <p>The asian jacked himself off furiously and his stretched hole flared. "Finish on me! Give me your cum!"</p>
  <p><em>"You're such a fucking dirty cum slut"</em> Cas jacked his own self off.</p>
  <p>"Yeah! Yeah! I'm a dirty fucking whore!"</p>
  <p>Kevin's room was filled with loud moans and degradations until he screamed as he came.</p>
  <p><em>"</em><em>UH! UH! OH FUCK!"</em> Castiel let a few drops sprinkle the twink's face before shoving his dick down his throat, making him swallow most of the contents of his balls.</p>
  <p>Kevin swallowed as much as he could and licked the last of the cum.</p>
  <p>"Yeah, that's it. Eat it, you fucking cum slut!" Cas put his foot on Kevin's head, pushing him down and forcing him to lick the last of the expelled off the carpet floors.</p>
  <p>Kevin wiped off his mouth as he stood. "You wanna shower first?"</p>
  <p>"I think you should first" Cas smiled humorously.</p>
  <p>Kevin chuckled. "Yeah. I'll see you at supper, Bro".</p>
  <p>"You sure you're gonna be hungry?"</p>
  <p>The sub laughed. "Probably not starving. I know I won't drink very much. How about you? You gonna eat dessert? You did just eat a lot of cake".</p>
  <p>Castiel laughed. "Fuck you, Brother!"</p>
  <p>"What do you think we were just doing? Preaching a service?" Kevin flipped him off.</p>
</div>
  </div></div>
<a name="section0004"><h2>4. 4</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Crowley walked casually down (Lebanon street). The Sunday morning air was a bit cool for the end of March in Lebanon. There were not very many people out, but there were people out. </p><p>The mob leader ran his right pointer and middle fingers along the back brim of his floppy, gray hat.</p><p>Castiel took the cue and stepped out from behind the building. He saw their victim immediately.</p><p>The guy was a few years younger than Cas. Judging by the (Lebanon high school) Letterman jacket, he was in good shape. Or maybe he sucked at the sport but barely made it? Either way, he was pretty hot. </p><p>'Focus, Cassie' he scolded himself. 'You wanna rob the guy, not fuck him'.</p><p>Although, that was the complete opposite.</p><p>Cas casually sped up to the dude. He looked at Crowley for confirmation.</p><p>He gave it to him.</p><p>Cas bumped into the dude expertly and sneakily took his wallet. " 'Scuse me" he 'apologized'.</p><p>Letterman turned to him. "No problem, man- HOLY SHIT!"</p><p>Cas was startled. "What?"</p><p>Letterman blushed furiously. "Nothing, nothing" he looked at the sidewalk.</p><p>Castiel smiled. "You're cute when you fumble".</p><p>Letterman blushed darker.</p><p>"Well, I think it's safe to say you walk on the other side of the street?"</p><p>Letterman looked up with wide, brown eyes. "What? No. This is my route home".</p><p>Castiel laughed and clasped his hands behind his back. "I meant you swing the other way. You're fumbling all over me, Jock". He pocketed the cash from the wallet.</p><p>"Uh, uh. No. I have a girlfriend. And I'm a mathlete".</p><p>"Oh yeah?" Cas pressed himself against Letterman. He slowly snuck his hand over his chest. "I can feel your heartbeat, Mathlete" he said softly. He looked at the sewn- in name over his hand. "Hopefully I'll see you around.... Dean". He dropped the now nearly- emptied wallet in the pocket.</p><p>Cassie backed up smoothly and turned on his heels. Dean watched him quietly sneak into the shadows and disappear.</p>
  </div></div>
<a name="section0005"><h2>5. 5</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Dean walked past his mother without a regard.</p>
<p>"Earth to Son, Earth to Son".</p>
<p>Dean playfully rolled his eyes with a loving smile. He grabbed her arms and pecked her on the lips. "Hi Mom".</p>
<p>Mary smiled. "What was that for?"</p>
<p>Dean spun once around her to the fridge. "I don't know".</p>
<p>"I'm making breakfast soon".</p>
<p>He closed the door empty handed.</p>
<p>Mary sat at the table and sipped her coffee. "I'm guessing you got laid last night?"</p>
<p>
  <em>"Aaawww, Mmooomm".</em>
</p>
<p>John busted out laughing from the living room.</p>
<p>"You wear a coat before it rained?" Mary asked.</p>
<p>Dean blushed even deeper. "Always, Mom".</p>
<p>"Good" she said. "Last time your father forgot a raincoat, we had you".</p>
<p>"Mom!"</p>
<p>John laughed harder than before, causing his newspaper to crumple in his hands.</p>
<p>Mary shrugged. "I'm just worried about you".</p>
<p>"I'm going to do homework!"</p>
<p>📗📘📙📚📔📒📑📓📕📖✏📝📏📐📎✂📋📁📂📃📄🍎</p>
<p>Dean forced himself to keep his mind at task, but he continued to think about the man who robbed him.</p>
<p>He was not mad, actually. He tried to be, but he thought it was funny. The guy knew he liked men immediately. The girl who always sees him naked has absolutely no idea.</p>
<p>Dean slammed his book shut and dropped the pencil. He had to see him again.</p>
<p>👀 👀 👀 👀</p>
<p>Cas felt something he had not felt in a long time about robbing someone: remorse. He didn't know why. Yeah the guy was fucking hot, but.... AAAAHHH! He didn't know why! He's robbed a bunch of guys he's thought was hot before. Why was this one different? And did he seriously hope he would see he again?</p>
<p>Yes, he did.</p>
<p>He wanted him. He wanted him bad. And not just the one time, like his brother was. He NEEDED him.</p>
<p>The kid was much younger than him. Okay, not MUCH younger, but a few years younger. He was still in school, for fuck's sake.</p>
<p>'His body was so tight. I bet he has a fucking sweet pussy- STOP! It's not going to happen, you're too different and he's got a broad!' </p>
<p>Cas told his large family in their nice, large living room goodnight and turned in.</p>
<p>He barely slept.</p>
<p> </p>
  </div></div>
<a name="section0006"><h2>6. 6</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Cas wished, but didn't think, he would see Dean again. Maybe he just needed to fuck him hard and good, then things could get back to normal? Or maybe he just needed time to forget him?  </p><p>He could also kill him? That would trick his mind into thinking he hated him. Why did he tell him he might see him again? </p><p>Motherfucker.</p><p>What the fuck was he supposed to do?</p><p>❔❓❔❓</p><p>He had no idea. He loved Lisa too death, but this guy....</p><p>It wasn't like anything was going to happen. The guy was older. He stayed in the shadows. Oh, and, he was a criminal.</p><p>So why did that turn him on more?</p><p>❔❓❔❓</p><p>Castiel stared at the big, bright moon from his window. He didn't want to lean on the sill. </p><p>No, the mob was no where near poor, but their house seemed like it. The house wasn't in a condemned condition, but it also wasn't the White House. </p><p>It also wasn't the only house. Of course, their small group was not the entire mob. But it's the only mob Cas has ever known.</p><p>Maybe Cas was the only mob Dean knew?</p><p>"Stop!" Cassie told himself out loud. </p><p>Was everything going to lead his mind back to Dean?</p><p>❔❓❔❓</p><p>Yes. </p><p>Dean finally decided. He got up from his seat and grabbed the letterman. Putting it on, he sneakily floated through the halls and out the front door. He shut it ever so softly.</p><p>Dean took a breath and turned on the flashlight he grabbed on his way out. He began his search for his thief.</p>
  </div></div>
<a name="section0007"><h2>7. 7</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Cas quietly and skillfully slit the man's throat with his knife from behind him. He caught him before he fell and dragged him into his garage.</p><p>Still alive, but barely, the man watched him beckon Benny in. Then he died.</p><p>"Try not to kill anybody else if they're here. But if you can't avoid it...." Cas shrugged.</p><p>The much larger man nodded. "Why don't we put him in the can?" Benny gestured with his head to the trash can.</p><p>"You're much stronger than I, would you....? " Cas trailed off.</p><p>Benny rolled his eyes. "Suuuure" he drawled in his southern accent. He picked the guy up and strung him on his shoulder like a sack of potatoes.He loved being the muscle. But he also hated being the muscle.</p><p>Meanwhile, Cas opened the front door and snuck into the house. It wasn't a billionaire's house, but it also wasn't the curb.</p><p>He quickly and quietly started taking anything that would or even probably would be considered valuable.</p><p>A few minutes later, Cas cringed at a loud noise of items crashing together. He went to the kitchen, where it came from. "Benny!" he hissed.</p><p>Benny stopped putting silver in his bag and looked at him with big, innocent eyes. "What?"</p><p>"Someone might be here, you oaf!"</p><p>"Sorry".</p><p>Cas sighed and headed for a bedroom.</p><p>The two got in, slit a guy's throat, stole everything they could, and got out in under ten minutes.</p><p>⌚⌚⌚⌚</p><p>This was a bad idea. Dean Archibald Winchester does not have had ideas. Much less acts upon them. It was stupid. It was dangerous. And somehow that excited him.</p><p>'What the fuck are you doing?' Dean asked himself. He didn't know.</p><p>Correction: he did know. He just didn't know why.</p><p>Correction again: he kinda did know why.</p><p>There was something about him. Like I said, the dude was incredibly hot.</p><p>But he was....</p><p>Dangerous. Dean's thief was dangerous. And that was exciting.</p><p>Dean finally reached the place where he was robbed.</p><p>'Congratulations, dumbass. Now what?' Dean thought.</p><p>Dean sighed. After waiting a half hour, he grabbed a piece of gum from his back pocket. After a few more minutes, he grabbed a pencil and notepad from his letterman. He wrote dark on a piece of paper and ripped it off the pad. He grabbed the gum, stuck it in the wall, and stuck the paper on it.</p><p>Before he left, he looked at once more, as if he would leap out of the fucking thing and fuck him like a dirty whore right there, in the streets.</p><p>Dean sighed again and went home.</p>
  </div></div>
<a name="section0008"><h2>8. 8</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>"Look at that one".</p>
<p>Cas rolled his eyes and reluctantly looked at the graffiti on the side of the building. "Yes, Benny. It's a very nicely painted large, cartoon breasts with a cock in the middle of them. Can we just go home now?"</p>
<p>"Fine. Fuck me for trying to enjoy the little things".</p>
<p>"Dammit" Cas cursed under his breath. "I'm sorry, Brother" he apologized. He put his hand on his shoulder. "You're right".</p>
<p>"It's immature".</p>
<p>"Quite".</p>
<p>"Have you ever tried something like that?"</p>
<p>Cas looked weirdly at his brother. "I came on a girl's tits before. When did you become so interested in art?"</p>
<p>Benny looked back. "School". His gaze returned to the vulgar wall.</p>
<p>"Studied art in Harvard. Although I'm not particularly fond of this.... masterpiece, I do appreciate the artist's attention to detail. I also like their use of the art and design principles and elements".</p>
<p>"Benny, I love you, you big- brained bastard" Cas started. "I'v known you for a while now. I'v never asked you though, why the fuck are you here?"<br/>Benny looked at him. "Being smart and having good grades is not enough to pay for the last two years of Harvard. And Ma and Pa didn't have enough money to support me. What's that?"</p>
<p>Cas looked at where he was pointing. He tilted his head and looked at the paper closer. After reading it, he smirked and took it off the wall.</p>
<p>"What's it read? And don't say 'nothing', because nothing is 'nothing' ".</p>
<p>"Alright then" Cas pocketed the note. "It's something". </p>
<p>"Brother!" </p>
<p>📃📃📃📃</p>
<p>"You know, I could just give you my number".</p>
<p>Dean stopped in his tracks. He turned to the deep, most beautiful voice he'd ever heard. </p>
<p>His mystery man wore the same dark gray, fuzzy trench coat and fedora.</p>
<p> </p>
<p>
  
</p>
<p> </p>
<p> </p>
<p>Dean smiled. "You came".</p>
<p>"Of course I did. Now you wanna.... cum together?"</p>
<p>Dean blinked at the invitation. "Um. That sounds quite nice, but I was thinking something a little slower?"</p>
<p>Cas tilted his head. "Like what?"</p>
<p>"A date, for starters".</p>
<p>"A date?"</p>
<p>"Yes, a date. It's how people get to know each other".</p>
<p>Cas chuckled. "You're mouthy".</p>
<p>Dean shrugged.</p>
<p>"Are you mouthy to your girlfriend, too?"</p>
<p>"Sometimes. But I usually get in trouble for that".</p>
<p>Cas smiled devilishly. "So she punishes you?"</p>
<p>Dean became warm despite the weather. ".... You want that date, or not?"</p>
<p>💋💋💋💋</p>
<p>"Why are you here with me, Dean?"</p>
<p>"Like I said on the note, I wanted to see you".</p>
<p>Cas sipped his free dark coffee. He glared at the barista, who kept looking at the phone on the wall. The barista shied away in fear. He pretended to make a cup of coffee. Cas knew if he flexed his muscles, he wouldn't dare touch the phone.</p>
<p>"Why did you want to see me? Do you want your money back?"</p>
<p> "No. No. Not at all" Dean started. "I figured if you tried that hard to get it, you needed it more than me".</p>
<p>Cas nodded. He looked at Dean expectantly. "So?"</p>
<p> Dean swallowed a sip of his white coffee. He was going to pay for both of their's when Cas didn't look. "So what?"</p>
<p> "Why did you want to see me?"</p>
<p>Dean looked at the sidewalk for a moment. "I don't know".</p>
<p>Cas set his cup down. "Yes, you do, Dean". He placed his palms flat on the table evenly, one on each side of the cup. "I do not like to be lied to, Boy. Understand?" His voice was stern and quiet. </p>
<p>Dean barely heard him, but dared not to asks him to repeat himself. "Yes Sir". He tingled everywhere.</p>
<p>"There is a reason for everything. Everyone has a motive for whatever they do. Now, I'm going to ask you one more time: why did you want to see me?"</p>
<p>Dean swallowed a lump in his throat. "You.... intrigued me. You excite me".</p>
<p>Cas looked at Dean for what sufficed for an uncomfortable amount of time. Finally he said something. "So, how old are you, Dean?"</p>
<p>Dean frowned. "I'm eighteen since February".</p>
<p>"Hm" Cas nodded. He sipped his coffee. "I am currently twenty-four".</p>
<p>Dean froze. He took a big swig of his coffee. "That won't be a problem, will it?"</p>
<p> "Why would it be? We're just getting coffee".</p>
<p>Dean looked at him and then back at his coffee. "Right".</p>
<p>"You haven't asked me why, yet".</p>
<p>" 'Why' what?"</p>
<p>"Deeeeeaan" Cas tilted his head, playfully disappointed. "I don't like it when someone pretends to not know something. That's lying. Try again".<br/>Damn. This man's voice could get Dean off alone. "Why did you take my money?"</p>
<p>"There. There's a good boy".</p>
<p>Dean nearly choked on his coffee.</p>
<p>"I come from a large group of very....dangerous people. We're respected. We're feared. We take what we want, and if someone objects...." Cas shrugged.</p>
<p>"Why?"</p>
<p>"Why? Well, I was taken in by them after some time on the streets. They give me a home, and everything I need. In exchange, I do this".</p>
<p>Dean let everything sink in for a moment. "Who are these people?"</p>
<p>Cas smiled. "That, my beautiful mathlete, is for another day". Cas drank the rest of his coffee. "Anymore questions?"</p>
<p>Dean took one more drink and let the last swallow sit. "One more for now: what's your name?"</p>
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<a name="section0009"><h2>9. 9</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>"Hey Baby".</p><p>"Hi Honey!" Mary called from the living room.</p><p>Dean heard Lisa laugh on the other side of the phone. "Hang on" he told her and hung the phone up. He went to his room and lied belly- down on his bed.</p><p>The couple had a long conversation. Well, many different conversations. Dean kept getting distracted.</p><p>"Why's your head all over the place, Baby?"</p><p>Dean thought longer and harder than he should have about that. "I don't know. I miss you. I need you".</p><p>There was a shorter pause on the other side. "What's wrong?"</p><p>"I- I want to try something I never have before. Something I'v always known I wanted, but never had the balls to do".</p><p>"Dean, you're scaring me". Lisa's voice was unnerved.</p><p>"Don't be. It'll be fun.... Now, your's or mine?"</p><p>🏠🏡🏠🏡</p><p>"Are you sure about this?" Lisa stood before Dean, stark naked -- save one brand new strap-on.</p><p>Dean nodded and smiled. "I'm a bit nervous, but more excited".</p><p>Lisa nodded. "You're sure you're parents don't mind?"</p><p>"I'm sure. I asked if it was okay if we made love here".</p><p>Lisa nodded again. "Are you absolutely positive --"</p><p>"Yes, Mistress".</p><p>Lisa smiled, pleased. She squirted the lube on her hand and rubbed it on the seven- inch rubber dick. "Turn around, Boy".</p><p>Dean's stomach flipped flopped and he got on his knees. He arches his ass up, full of anticipation.</p><p>Lisa kneeled behind Dean and lined up with his thoroughly - lubed hole.</p><p>"Please, Mommy".</p><p>That pushed her over the edge and she shoved into Dean.</p><p>"AAHH!"</p><p> Lisa stopped and pulled out a little.</p><p> "No, please! Please Mommy, I need my pussy filled".</p><p> Lisa stopped. "Are you okay? It doesn't hurt?"</p><p> "No, Mommy. Please, fuck my hole. Make my pussy cum".</p><p>Lisa shoved in more. "Dirty boy".</p><p>"Mmmm".</p><p>More. "You like being dominated, huh? Having someone push your buttons until you scream? But you can't cum until they say so, huh?"</p><p>"Yes, Mistress. Please. I need it deeper".</p><p>Dean couldn't see Lisa's confused- turned- adventurous look.</p><p>The dominant shoved in all the way.</p><p>"FUCK!"</p><p>Lisa pulled out almost completely. "I'm so sorry, Baby! Are you ok!? Maybe we can get, um, some ice!?"</p><p>"Fuck. No, don't stop! Don't stop! Don't stop! Please, Mommy!"</p><p>Lisa did stop. "It doesn't hurt?"</p><p>"It did when you shoved it in like you were stabbing me!"</p><p> ".... Dean, I'm confused".</p><p>"Ease it in gently. Start when I ask. Start slow. Then when I... get into it more, BANG MY PROSTATE INTO MY THROAT!"</p><p>Lisa laughed. She gripped onto Dean and thrusted deep into him.</p><p>"Hm!" Dean let out a pathetic whimper.</p><p>Lisa repeated the action and Dean gasped long and hard to suck in an orgasm.</p><p>What? You can't fucking suck in an orgasm. Especially with no contact on your dick.</p><p>Anyway, Dean relaxes as best he can- which is not very much- and Lisa thrusted gently again.</p><p>"Mm. Yeah".</p><p>"Yeah? You like that?"</p><p>"Yeah, Mommy" Dean reached back and grabbed Lisa's thigh. He hammer fisted the bed hard when she thrusted again. "I'm ready".</p><p>Lisa grabbed his shoulders. "Ready for what? Tell me what you're ready for".</p><p>"This. Please, fuck me in the ass".</p><p>Lisa took a breath. She began slowly.</p><p>"Ha- ah!"</p><p>"You okay?" Lisa didn't stop.</p><p>"Yes. Fuck yes".</p><p>Lisa smirked and forced herself not to pound Dean into the mattress. "Who's your mommy?"</p><p>"You are, Lis. You're my mommy!"</p><p>Lisa fucked him harder. "You like that?"</p><p>"Yes! Yeah, Mommy! Fuck me!"</p><p>Lisa did. As hard as she could. She loved the effect on Dean.</p><p>"F-- FUCK! OH GOD!" Dean tried to find something to claw, but couldn't settle. Lisa found his prostate-- something he's only been able to do.</p><p>"FUCK! YES! YES! THERE! RIGHT THERE! OH MY-- FUCK!"</p><p> "It feels that good?" Lisa was surprised, for lack of a better word. She slowed down.</p><p> "Higher! Like before! Higher!"</p><p>Lisa angled her penis higher and was startled at Dean's scream. She smirked. "Did I find it?" She lowered her angle again.</p><p>"Yes! Yes, Mistress! Please! Pound my prostate into my throat!"</p><p>Lisa was so turned on. "You want me to fuck your prostate? Hm? Is that what you want?" She continued to fuck his ass without heading home.</p><p> </p><p>
  
</p><p> </p><p>"Yes, Mommy! Fuck my prostate!"</p><p>"Ask nicely, Dean" she spanked him. "Use your manors".</p><p>Dean felt like crying. He was desperate for Lisa to find his g-spot again. "Please, Mommy! PLEASE! I need it! I need it! Please, make my pussy cum! AHH!"</p><p>"Good boy, Dean" she angled herself in that way again.</p><p>"I'm gonna cum! Please Mistress, let me cum!"</p><p>Lisa gripped Dean's balls and squeezed them tight. "No. You're gonna cum from your pussy, remember?"</p><p>Dean moaned. "Please! Please!"</p><p>"I. Said. No".</p><p>Dean was left a helpless moaning mess. Needing release. Begging for Lisa to let him cum. Of course she didn't.</p><p>Lisa came from the intensity on her clit. Her moans of ecstasy mocked Dean in his pathetic state. She took pity on him and let go of his balls.<br/>Dean saw stars as he soaked his own sheets. Nothing in the world existed except for his pleasure.</p><p>Although, he was very disappointed Lisa didn't make him cum from his ass.</p><p> </p>
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